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#$Date: 2025-08-19 09:12:48 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301798 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/81/2018111.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2018111
loop_
_publ_author_name
'Hu, Qiao-Sheng'
'Zhang, Xiu-Zhi'
'Luo, Shu-Fen'
'Sun, Yu-Hui'
'Du, Zi-Yi'
_publ_section_title
;
 Two polymorphs of (2-carboxyethyl)(phenyl)phosphinic acid
;
_journal_coeditor_code           SF3148
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o195
_journal_page_last               o197
_journal_paper_doi               10.1107/S0108270111013163
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C9 H11 O4 P'
_chemical_formula_moiety         'C9 H11 O4 P'
_chemical_formula_sum            'C9 H11 O4 P'
_chemical_formula_weight         214.15
_chemical_name_common            '2-carboxyethyl(phenyl)phosphinc acid'
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.1741(15)
_cell_length_b                   8.7308(19)
_cell_length_c                   19.844(4)
_cell_measurement_reflns_used    1679
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.72
_cell_measurement_theta_min      2.55
_cell_volume                     1069.7(4)
_computing_cell_refinement       'SMART (Bruker, 2008)'
_computing_data_collection       'SMART (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_molecular_graphics
;
DIAMOND (Brandenburg, 1999)
;
_computing_publication_material  'SHELXTL (Bruker, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0259
_diffrn_reflns_av_sigmaI/netI    0.0353
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            5593
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.55
_exptl_absorpt_coefficient_mu    0.243
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6793
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2008)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.330
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.178
_refine_diff_density_min         -0.215
_refine_ls_abs_structure_details 'Flack (1983), 989 Friedel pairs'
_refine_ls_abs_structure_Flack   0.11(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     133
_refine_ls_number_reflns         2422
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0499
_refine_ls_R_factor_gt           0.0370
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0465P)²+0.0144P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0831
_refine_ls_wR_factor_ref         0.0898
_reflns_number_gt                1977
_reflns_number_total             2422
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sf3148.cif
_cod_data_source_block           II
_cod_original_sg_symbol_H-M      P212121
_cod_database_code               2018111
_cod_database_fobs_code          2018111
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
P P1 0.37137(10) 0.30994(5) 0.07762(2) 0.03642(15) Uani d . 1 1 . .
C C1 0.2943(4) 0.3038(3) 0.16448(10) 0.0424(5) Uani d . 1 1 . .
C C2 0.4255(5) 0.3675(3) 0.21432(11) 0.0573(7) Uani d . 1 1 . .
H H2A 0.5568 0.4124 0.2026 0.069 Uiso calc R 1 1 . .
C C3 0.3614(6) 0.3644(4) 0.28125(12) 0.0756(9) Uani d . 1 1 . .
H H3A 0.4495 0.4071 0.3143 0.091 Uiso calc R 1 1 . .
C C4 0.1681(7) 0.2984(5) 0.29860(14) 0.0897(11) Uani d . 1 1 . .
H H4A 0.1255 0.2962 0.3435 0.108 Uiso calc R 1 1 . .
C C5 0.0382(6) 0.2362(5) 0.25059(16) 0.1031(13) Uani d . 1 1 . .
H H5A -0.0931 0.1924 0.2630 0.124 Uiso calc R 1 1 . .
C C6 0.0992(5) 0.2372(4) 0.18286(13) 0.0735(9) Uani d . 1 1 . .
H H6A 0.0099 0.1936 0.1504 0.088 Uiso calc R 1 1 . .
C C7 0.2817(4) 0.4866(2) 0.03997(11) 0.0433(5) Uani d . 1 1 . .
H H7A 0.3459 0.4959 -0.0045 0.052 Uiso calc R 1 1 . .
H H7B 0.1257 0.4827 0.0343 0.052 Uiso calc R 1 1 . .
C C8 0.3389(4) 0.6269(2) 0.08058(10) 0.0439(5) Uani d . 1 1 . .
H H8A 0.4884 0.6185 0.0952 0.053 Uiso calc R 1 1 . .
H H8B 0.2488 0.6294 0.1206 0.053 Uiso calc R 1 1 . .
C C9 0.3113(4) 0.7760(2) 0.04301(11) 0.0387(5) Uani d . 1 1 . .
O O1 0.6226(3) 0.31246(18) 0.08088(7) 0.0472(4) Uani d D 1 1 . .
H H1A 0.685(4) 0.323(3) 0.0452(7) 0.057 Uiso d D 1 1 . .
O O2 0.2784(3) 0.17650(16) 0.03892(7) 0.0491(4) Uani d . 1 1 . .
O O3 0.3148(3) 0.79083(17) -0.01724(7) 0.0476(4) Uani d . 1 1 . .
O O4 0.2882(4) 0.89173(16) 0.08613(8) 0.0615(5) Uani d D 1 1 . .
H H4B 0.288(5) 0.9748(18) 0.0667(13) 0.074 Uiso d D 1 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O2 P1 O1 . . 114.33(10) ?
O2 P1 C1 . . 111.47(10) ?
O1 P1 C1 . . 103.07(10) ?
O2 P1 C7 . . 109.47(9) ?
O1 P1 C7 . . 108.19(12) ?
C1 P1 C7 . . 110.09(11) ?
C6 C1 C2 . . 119.0(2) ?
C6 C1 P1 . . 119.83(18) ?
C2 C1 P1 . . 121.12(19) ?
C3 C2 C1 . . 120.4(3) ?
C3 C2 H2A . . 119.8 ?
C1 C2 H2A . . 119.8 ?
C4 C3 C2 . . 119.9(3) ?
C4 C3 H3A . . 120.1 ?
C2 C3 H3A . . 120.1 ?
C5 C4 C3 . . 120.4(3) ?
C5 C4 H4A . . 119.8 ?
C3 C4 H4A . . 119.8 ?
C4 C5 C6 . . 120.9(3) ?
C4 C5 H5A . . 119.6 ?
C6 C5 H5A . . 119.6 ?
C1 C6 C5 . . 119.4(3) ?
C1 C6 H6A . . 120.3 ?
C5 C6 H6A . . 120.3 ?
C8 C7 P1 . . 113.70(15) ?
C8 C7 H7A . . 108.8 ?
P1 C7 H7A . . 108.8 ?
C8 C7 H7B . . 108.8 ?
P1 C7 H7B . . 108.8 ?
H7A C7 H7B . . 107.7 ?
C7 C8 C9 . . 114.20(17) ?
C7 C8 H8A . . 108.7 ?
C9 C8 H8A . . 108.7 ?
C7 C8 H8B . . 108.7 ?
C9 C8 H8B . . 108.7 ?
H8A C8 H8B . . 107.6 ?
O3 C9 O4 . . 124.01(19) ?
O3 C9 C8 . . 125.54(19) ?
O4 C9 C8 . . 110.42(17) ?
P1 O1 H1A . . 116.0(19) ?
C9 O4 H4B . . 112(2) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
P1 O2 . 1.5087(15) yes
P1 O1 . 1.5527(17) yes
P1 C1 . 1.789(2) ?
P1 C7 . 1.801(2) ?
C1 C6 . 1.386(4) ?
C1 C2 . 1.394(3) ?
C2 C3 . 1.386(3) ?
C2 H2A . 0.9300 ?
C3 C4 . 1.369(5) ?
C3 H3A . 0.9300 ?
C4 C5 . 1.358(5) ?
C4 H4A . 0.9300 ?
C5 C6 . 1.396(4) ?
C5 H5A . 0.9300 ?
C6 H6A . 0.9300 ?
C7 C8 . 1.508(3) ?
C7 H7A . 0.9700 ?
C7 H7B . 0.9700 ?
C8 C9 . 1.510(3) ?
C8 H8A . 0.9700 ?
C8 H8B . 0.9700 ?
C9 O3 . 1.203(2) yes
C9 O4 . 1.331(3) yes
O1 H1A . 0.810(10) ?
O4 H4B . 0.821(10) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O1 H1A O2 4 0.810(10) 1.767(11) 2.566(2) 169(3)
O4 H4B O2 1_565 0.821(10) 1.847(11) 2.658(2) 169(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9462327
2 PubChem 11287340
